Have Yourself A Merry Little Winchester Christmas
by x.x.x.RaindropsOnRoses.x.x.x
Summary: A Moose. A Squirrel. An Angel. Team Free Will search for the perfect tree and go on a short holiday road trip, for once, nothing goes wrong, but that doesn't mean there won't be some... ahem, odd twists and turns along the way. DEDICATED TO AMBER.


**Have Yourself A Merry Little Winchester Christmas**

 **PART ONE: ROAD TRIPPING**

A/N: So, here it is, my very first Supernatural fic, and just in time for Christmas! This one is for a very, very special Queen Squirrel, AKA, Amber. Many of you probably know her on Twitter as DestielLove1 and if you don't know this gem, you need to go follow her ASAP.

I hope you all enjoy this one shot, and keep in mind for the purposes of this fic, that neither Crowley nor Rowena are dead (What? It's Christmas and this _is_ Supernatural after all. It was a Christmas resurrection miracle, lol). And if anyone dislikes any member of the beloved Team Free Will, please note that this story is not for you.

To all of you who read this, I wish you and your families a very Merry Christmas, and a very happy, safe New Year.

Much love,  
Donna.

"Remind me again why we're driving all the way to Colorado to buy a Christmas tree."

Dean Winchester huffed out an exasperated sigh and gripped the steering wheel of his beloved Impala even tighter, his irritation evident in his rigid posture. "For the last time, Cas," he huffed out in is usual gruff tone, an acerbic comment undoubtedly prickling on the tip of his tongue. With a deep breath and and a roll of his eyes, Dean pushed back down his retort and continued to stare down the virtually empty Interstate 70. "There's this place on the edge of a spruce forest, where Bobby had one of his cabins- It was actually one of his favourite places. Anyway, there was this one year he took us there for a couple of days, you know, over Christmas. He took us out to get the tree, even cut it down himself, and Sammy and I made these cardboard Devil's traps and spare bullets to decorate it with…" He trailed off for a moment, lost in the thoughts of one his rare, yet treasured, memories of the Holidays.

"Yes, I heard you the first seven times, Dean," Cas said in his deeply mysterious yet monotone voice. "What I _don't_ understand is why we're going there _now_."

Dean's eyes flicked up to the rearview mirror and back down to the road again. "Sammy and me, we were thinking that since this is the first Christmas that we've really been in a good place since before Bobby died, not to mention all together in the one place at the same time… well we just thought that it would be great to honour Bobby- make _new_ memories, _good ones_ , so we have something to hold onto when everything inevitably implodes yet again, and our lives fall to crap," he explained, pausing for a second as though waiting for the Angel to reply.

He didn't.

"Anyway," Dean continued after a beat, "It's you, me, Sammy and Jack now. We've wanted a real family Christmas forever, and now we can have that. Just the four of us, in the bunker."

Castiel remained silent for several minutes, as though trying to process this new information had rendered him unable to speak. "Oh," he deadpanned eventually. "I understand. Thank you."

Dean turned to his right, a deep frown marring his handsome face. " _Seriously_?" he shook his head and let out a miffed puff of air. "That's all you have to say about it? ' _I understand…?_ '"

"That's what I said. What else do you want from me, Dean?"

"Well okay, _Asstiel_ , since you asked—

Cas shot Dean a highly indignant look before turning his attention to the passing greenery outside his window, his eyes firmly locked somewhere in the distance as he feigned hurt feelings.

The elder Winchester's eyes trained on the angel for a few lingering seconds before he too, turned his away and went back to staring headlong into the highway lines before him. The instant that he did though, Cas flared his nostrils at the Metal cover of _God Rest Ye Merry Gentlemen_ that was blaring through the stereo, and flicked the radio over to another station, where the sound of a grating bass and clashing drums was immediately replaced by a piano and a woman singing _O' Holy Night_ in an operatic voice— the kind that gives you the chills, and not in the good way.

With a sudden and near-deafening squeal of the brakes, a sharp, violent swerve to the right and enough burning rubber to create a waft of unpleasantly fragrant smoke, Dean swerved the Impala off the road, pulling it to a screeching halt just off the highway. If the wild look in his eyes was anything to go by, he was angrier than a cut snake and was going to be as delicate about his beef as a bull in a china shop.

Nobody messed with his music and got away with it. _No one_.

 _Not even Sam_.

"Is something the matter, Dean?" Castiel questioned as casually as ever, his slightly smug expression giving away the fact that he was purposely provoking the Hunter beside him.

"Oh I don't know, you tell me," Dean replied tersely, flipping the station back to his original station in a slightly more forceful way than was necessary. "What's my one rule, man?"

"I don't believe I know to what you are referring."

Dean scoffed at that. "You're unbelievable!"

"Yes, I know," Cas affirmed, squinting his eyes warily in Dean's direction.

"No that's not—

"Of that I am _very_ aware," the angel continued. "You people are so _predictable_ and… _ordinary_. "

"Anyway," Dean said, raising his voice over the top of Castiel. "Nobody, not even Sam, is allowed to mess with my music. Ever. You don't get to come in here and put your paws all over my music—

"I'm an Angel, you ass. I don't have _paws_ —

"That's besides the point!" Dean was very nearly popping a blood vessel at this point. "I mean, do I go into your secret dungeon at the bunker, in your own personal space and play with all your angel toys and crap? NO!"

Cas regarded Dean for a few beats, obviously unsure about the direction the conversation was taking, "Of course not," he said, his tone rough and uneven, yet resolute. "That would be strange, even by your standards."

"Riiiight." Dean's ever skeptical tone had returned, as he once again turned away from the source of his irritation. "One rule, man. _ONE._ Driver picks the music—

"Shotgun shuts his cakehole," Cas finished, unimpressed by the whole dang affair. "Yeah, I'm pretty sure I got it, thanks."

 _Oh, the sarcasm_.

"Speaking of shotgun," Came a voice from the back, the third wheel who's presence in the car appeared to have been long since forgotten. "How is it that an angel, no offence, Cas, gets to ride shotgun and your own brother is forced to sit in the back like a captive, and listen to the both of you argue like an old married couple?"

Both Dean and Castiel jumped in their seats, startled by the sound of Sam's voice. The latter turned to face the younger Winchester only to find him wearing perhaps the most bored expression he had ever seen, and staring back with giant, puppy-eyes.

"Well," Cas began, "Your br—

"Well," Dean said far too loudly for it to _not_ be weird. "You're the sucker who lost at Rock, Paper, Scissors, bro."

"Yeah, maybe so, but it's not even like I knew what I was playing for, is it?" Sam huffed at his brother.

Dean shrugged unapologetically. "Oh," he said, tone flat. "Well I guess now you do."

Sam, who was still so clearly unimpressed by Dean's half-answer, pressed on. "Yeah, but _how_ did you win? You've only ever beaten me once, ever. I mean, man- you _always_ go with the scissors!"

"Call it a Christmas miracle," Dean grinned mischievously as he pulled back out onto the road, his charming demeanour back firmly in its place.

This time it was Castiel who scoffed. "Hardly. Your brother here played against my weaknesses. He told me that if I read your mind and and told him what moves to make ahead of time… that he'd let me sit in the front."

"You _cheated_?" Sam gasped disbelievingly. "At Rock, Paper, Scissors? _Come on_ , dude." He shot Dean an unimpressed yet unsurprised expression and glanced sideways at a very guilty looking Cas.

When Dean avoided eye contact with either of them, Cas took it upon himself to continue. "For the record, Sam, I only did it because I let my selfish desire to ride shotgun, temporarily compromise my logical reasoning. As it turns out, it wasn't worth the fuss after all. This _sucks_."

Sam snorted at that, and so did Dean, the presence of his brother having seemingly returned some of his Christmas spirit. For a brief second, the brother's eyes met in the rearview mirror, a slight twinkle playing in their eyes that could only mean one thing…

"Jerk."

"Bitch."

"Assbutt," Cas added, looking extremely pleased with himself.

A booming laugh reminiscent of a certain Padalecki escaped Sam, and Dean rolled his eyes for what seemed like the hundredth time that morning. Cas ignored them both.

 _Another year, another tree. But this year you won't be with me…_

"Aw, I love this song!" Dean exclaimed as Christmas by the Phone came over the radio. "Let's crank this baby up!"

And as Team Free Will sped along the interstate, any outsider would see them as three carefree brothers, simply out on a holiday road trip. The flannel-covered driver belting out a tune, the giant drumming to the beat stuffed awkwardly into the back seat, and the silent observer- a baby face in a trench coat, watching on thoughtfully with a small, genuine smile gracing his angelic features.


End file.
